Vat dyes and making the same.



UNITED STATES PATENT OFFICE ARTHUR L'U'TTRINGHAUS, OF MANNHEIM, AND WILHELM BRAREN, 0F LUDWIGS- HAFEN-ON-THE-RHIIYE, GERMANY, ASSIGNORS TO BADISCHE .AN'ILIN & SODA FABRIK, OF LUDWIGSHAFEN-ON-THE-RHINE, GERMANY,- A CORPORATION.

VAT DYES AND MAKING THE SAME.

1 935,023. No Drawing.

Patented Aug. 6, 1912.

To all whom it may concern: 7

Be it known that We, ARTHUR LI'iTTRING- I-IAUS and WILH LM BRAREN, subjects the first of the King of Prussia and the second of the King of Bavaria, residing, respectively, at Mannheim and Ludwigshafen-onthe-Rhine, Germany, have invented new and useful Improvements in Vat Dyes and Making the Same, of which the following is a specification.

We have found that those anthracridones in which two anthraquinone residues (either substituted or not) are joinedtogether by an acridone ring and in which the carbonyl group of the acridone ring stands in the position of a gamma diketone to the carbonyl of an anthraquinone residue, as illustrated by the formula can be converted into valuable new vat coloring matters by treatment with hydra- Our new coloring matters are characterized by consisting, when (11' of dark powders which are practically insoluble in the ordinary organic solvents, they yield bluish red solutions in concentrated sulfuric acid, ,brown vats .with. alkaline hydrosulfite, and dye cotton from gray to violet shades of excellent fastness.

The following examples will serve to caustic soda) and 250 parts of cresol. Then filter 05 the reaction product, which separates out in the form of small dark crystals.

With alkaline hydrosulfite the new coloring matter gives a brown vat which dyes cotton gray shades of excellent fastness.

Wash them with cresol and alcohol and dry Example 2: Heat together, for 8 hours, at I from 120 to 130 (3., 5 parts of the anthracridone obtainable from 3-amino-4-chlordiphenyl-ketone-EZ'-carboxylic acid and 1- chlor-anthraquinone-2-carboxylic acid (see the aforesaid British Patent No. 894/11), 5 parts of hydrazin hydrate and 250 parts of cresol. When the reaction product is cold, filter off the coloring matter, wash it with cresol and alcohol, and dry it. A reddish black powder is obtained which is practically insoluble in the ordinary organic solvents, but yields a brownish vat with alkaline hydrosulfite, which vat colors cotton brown shades which, upon oxidation in the air, give rise to a full violet of excellentfastness. It yields a bluish 'red solution in concentrated sulfuric acid.

In a similar manner, vat coloring matters can be obtained from other anthracridones having the aforesaid structure.

Now what we claim is 1. The process of producing vat coloring matters of the anthraquinone series by condensing with hydrazin a dianthraquinoneacridone in which the carbonyl group of the acridone ring stands in the position of a gamma'diketone to the carbonyl of an anthraquinone, residue.

2. The process of producing vat coloring matter of the anthraquinone series by condensing hydrazin hydrate with the anthracridone obtainable from 3-amino-4-methyldiphenyl-ketone-2-carboxylic acid and 1- chlor-anthraquinone-2-carboxylic acid.

3. The new vat coloring matters which can be obtained by treating with hydrazin a dianthraquinone-acridone in which the carbonyl group of the acridone ring stands in the position of a gamma diketone to the carbonyl ofan anthraquinone residue, which new colorlng matters consist, when.

dry, of dark powders which are practically insoluble in the ordinary organic solvents,

whichyield bluish red solutions in c0ncen-,

line hydrosulfite, and dye cotton from gray to violet shades of excellent fastness.

4. The new vat coloring matter of the anthraquinone series which can be obtained by condensing hydrazin hydrate with the anthracridone obtainable from 3-amino-4- methyl-diphenyl-ketone 2 carboxylic acid and 1 chlor anthraquinone 2 carboxylic acid, which new coloring matter can .be obtained in the form ofdark crystals which are insoluble in the ordinary organic solvents, but yield an intense bluish red solution in concentrated sulfuric acid and a broyvn vat with alkaline hydrosulfit'e and dye cotton gray shades of excellent fastness. 15

ARTHUR LUTTRINeH Us. WILHELM BRAREN.

Witnesses:

ERNEST G. EHRHARDT, J08. PEIFFER. 

